WO2004058896A1 - Composition de resine de silicone - Google Patents

Composition de resine de silicone Download PDF

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Publication number
WO2004058896A1
WO2004058896A1 PCT/JP2003/016751 JP0316751W WO2004058896A1 WO 2004058896 A1 WO2004058896 A1 WO 2004058896A1 JP 0316751 W JP0316751 W JP 0316751W WO 2004058896 A1 WO2004058896 A1 WO 2004058896A1
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Prior art keywords
group
component
parts
weight
composition
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PCT/JP2003/016751
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English (en)
Japanese (ja)
Inventor
Hiroyuki Kayaki
Hideki Ueno
Ikuo Takahashi
Hideshi Tomita
Original Assignee
Henkel Loctite Corporation
Nisshinbo Industries, Inc.
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Application filed by Henkel Loctite Corporation, Nisshinbo Industries, Inc. filed Critical Henkel Loctite Corporation
Priority to AU2003292811A priority Critical patent/AU2003292811A1/en
Priority to EP03768240A priority patent/EP1584660A4/fr
Publication of WO2004058896A1 publication Critical patent/WO2004058896A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups

Definitions

  • the present invention relates to a silicone resin composition and a cured product thereof, and more particularly to a cured product having a high elongation and excellent heat resistance, oil resistance, water resistance and chemical resistance in the field of, for example, an automobile. It is intended to provide a silicone resin composition and a cured product thereof.
  • the present invention provides a silicone resin composition that gives a silicone cured rubber having high elongation, heat resistance, oil resistance, and chemical resistance, which are characteristics particularly required for automotive applications.
  • the purpose is to provide things.
  • the component (b) 0.1 to 200 parts by weight of the component (b): the carbodiimide compound, and 100 parts by weight of the component (c) ):
  • This relates to a silicone resin composition mixed with an organic silicon crosslinking agent.
  • the component (b) 0.1 to 200 parts by weight of the component (b): the carbodiimide compound, and 100 parts by weight of the component (a): the OH group-containing polysiloxane.
  • d): relates to a silicone resin composition mixed with an amino group-containing silane compound.
  • the present invention is a composition in which at least one of the component (C) and the component (d) is mixed with the component (a) and the component (b) as described above.
  • a reaction may occur when each component is mixed and between mixing and before use. .
  • any state is meant as long as each component is "mixed”.
  • all the components may be divided into at least two parts and used as a composition set.In such a case, the mixture is also referred to as a mixture when the compound exists as it is, It may be in any state when those reactions have progressed.
  • the (H) -containing polysiloxane of component (a) is a polysiloxane having two or more OH groups.
  • Xane is preferably a liquid in order to be mixed with other components.
  • a preferred OH group-containing polysiloxane has the general formula (I):
  • RR 2 and R 3 in independently of one another H, showed an OH group or a fluorine good monovalent substituted hydrocarbon group, where, R 1 Contact And R 2 may be different groups on different Si atoms, and R 4 represents H or a monovalent hydrocarbon group optionally substituted with fluorine.
  • R 4 is a monovalent hydrocarbon group which may be substituted by fluorine
  • at least one of all R 1 and R 2 and R 3 is an OH group.
  • n is selected so that the viscosity at 25 ° C. becomes a desired viscosity, and is usually selected so as to be 10 to 100, 000, OOOcp.
  • Examples of the monovalent hydrocarbon group which may be substituted with fluorine which R 1 to R 4 may take include a linear or cyclic aliphatic hydrocarbon group having up to 20 carbon atoms, an aryl group, and these Examples include groups in which at least one hydrogen is replaced with fluorine.
  • OH group-containing polysiloxane is a ⁇ H group-terminated polysiloxane in which R 3 is a ⁇ H group and R 4 is H and both terminals are OH groups, wherein R 1 and R 2 Is preferably H or a monovalent hydrocarbon group optionally substituted by fluorine.
  • R 1 and R 2 are methyl groups, or one is a methyl group and the other is a phenyl group or H are preferred.
  • R 1 and R 2 are both methyl groups.
  • OH group-containing polysiloxane may be used alone or as a mixture of two or more.
  • the viscosity (or n in the formula (I)) of the OH group-containing polysiloxane used in the present invention is not particularly limited as long as it is a liquid within a range in which other components can be mixed, and is usually 10 cp to: 10,000,000,000 cp. And particularly preferably in the range of 100 to 1,000,000, more preferably in the range of 1,000 to 100,000.
  • n is selected to have such a viscosity.
  • the carbodiimide compound is a known compound, and a compound synthesized by a generally well-known method can be used. For example, it can be synthesized by using an organophosphorus compound or an organometallic compound as a catalyst and subjecting various isocyanate compounds to a decarboxylation condensation reaction in a solvent-free or inert solvent.
  • aromatic diisocyanate, aliphatic diisocyanate, alicyclic diisocyanate and a mixture thereof can be used as the organic diisocyanate as a raw material for synthesizing the polycarboimide compound.
  • the polycarboimide obtained by such a reaction has an isocyanate group at a terminal, and in the present invention, even such a polyisocyanate group containing a terminal isocyanate group has a modified terminal isocyanate group. Either polycarboimide can be used.
  • a compound in which the terminal isocyanate is modified by reacting a monoisocyanate compound with the terminal of a polycarboimide synthesized from diisocyanate can be used.
  • a monolithic material for sealing the terminal of polycarboimide is used.
  • the socyanate include phenyl isocyanate, tolyl isocyanate, dimethyl phenyl isocyanate, cyclohexyl isocyanate, butyl isocyanate, naphthyl isocyanate, and methyl isocyanate.
  • the decarboxylation condensation reaction of the organic dissociate proceeds in the presence of a carpoimidization catalyst.
  • a carpoimidization catalyst examples include, for example, triphenyl-2-phospholene-1-oxoxide and 3-methyl-1-oxide.
  • Hydrocarbon solvents such as tetrahydrofuran, dioxane, diethylene glycol dimethyl ether; ketone solvents such as 2-methylcyclohexanone, cyclohexanone, cyclohepnone, 2,4-dimethyl-3-heptanone Aromatic hydrocarbon solvents such as benzene, toluene and ethylbenzene; and acetate solvents such as 2-methoxyethyl acetate and diethylene glycol monomethyl ether acetate.
  • ether solvents such as tetrahydrofuran, dioxane, diethylene glycol dimethyl ether
  • ketone solvents such as 2-methylcyclohexanone, cyclohexanone, cyclohepnone, 2,4-dimethyl-3-heptanone
  • Aromatic hydrocarbon solvents such as benzene, toluene and ethylbenzene
  • acetate solvents such as 2-methoxye
  • polycarboimide examples include V-O2, V_O4, V-O6, E-O1, E-O2 available from Nisshinbo Co., Ltd. under the trade name of "Carpolite”. And oil-based types such as V-01, V-03, V-05, V07, V09 and the like.
  • V-01, V-03, V-05, V07, V09 and the like oil-based types such as V-01, V-03, V-05, V07, V09 and the like.
  • the structure of the main chain, the structure of the terminal group, the ratio of the carbodiimide group contained in one molecule, the dilution ratio, and the like are different, and can be appropriately selected and used.
  • carbodiimide compound one kind may be used alone, or two or more kinds may be used in combination.
  • Component (b) The amount of the carbodiimide compound to be used, even if it is used in a very small amount, will improve the physical properties of the cured resin, the engine oil resistance, and the long life coolant resistance, but the effect will be substantially clear
  • the amount is preferably at least 0.1 part by weight based on 100 parts by weight of the component (a): OH group-containing polysiloxane. More preferably, the amount is 1 part by weight or more.
  • the component (b) can be used in a large amount as long as it is compatible with the component (a), but usually not more than 200 parts by weight per 100 parts by weight of the component (a). Is preferably 100 parts by weight or less, more preferably 50 parts by weight or less. Therefore, as a usual use range, the component (a) is used in an amount of 100 to 200 parts by weight with respect to 100 parts by weight of the component (a).
  • an organic silicon cross-linking agent those known as curing agents for condensed one-part liquid silicone rubber are suitably used. These curing agents are used for one-pack silicone rubber and cure and condense with moisture to remove carboxylic acids, alcohols, oximes, amines, amides, aminoxys, ketones, hydrogen molecules or water. Compounds that release.
  • X 1 is each independently H, ⁇ H, alkoxy, oxymo, alkenoxy, amino, amido, aminoxy or acyloxy.
  • X 2 is each independently a hydrocarbon group having up to about 20 carbon atoms, for example, Ci Cz. Alkyl group, C 2 ⁇ C 2. It is an alkenyl group, an aryl group having up to 20 carbon atoms or a fluoroalkyl group.
  • a is 0, 1 or 2, preferably 0 or 1.
  • X 1 is preferably a hydrolyzable group, an alkoxy group, an oxymo group, an alkenoxy group
  • R is an alkyl group) and a dialkylaminooxy group (such as a dimethylaminooxy group).
  • X 2 is preferably ( ⁇ ⁇ (: 8 alkyl, C 2 -C S alkenyl, Hue group, more preferably a methyl group, Echiru group, a vinyl group.
  • a cyclic aminoxysiloxane in which an aminoxy group is bonded to Si of the cyclic siloxane is also mentioned.
  • each R may be the same or different and is an alkyl group such as methyl or ethyl, or an aryl group; (1 is about 3 to 10; p is 0 ⁇ p ⁇ Q —2, preferably 0 ⁇ p ⁇ Q—3.]
  • each R is the same or different and is an alkyl group such as methyl or ethyl, or an aryl group;
  • Q is about 3 to 10; and
  • p is 0 ⁇ p ⁇ q — 1, preferably 0 ⁇ p ⁇ q—2.
  • Q is typically 4, where p is 0, 1 or 2. These can be used in mixtures.
  • R bonded to the Si atom and R bonded to the N may be the same or different from each other, and are preferably a methyl group, an ethyl group or a phenyl group, and more preferably Is at least R bonded to Si is a methyl group.
  • organic silicon crosslinking agents examples include methyltriacetoxysilane, vinyltriacetoxysilane, methyltrialkoxysilane (e.g., methyltrimethoxysilane), vinyltrialkoxysilane (e.g., vinyltrimethoxysilane), methyltri (methylethylketoximo).
  • Silane biertri (methylethylketoximo) silane, tetra (methylethylketoximo) silane, methyltri (cyclohexylamino) silane, methyltri (isopropenoxy) silane, vinyltri (isoprobenoxy) silane, dimethyl
  • amidosilane eg, methylcarbonyl N-ethylaminodimethylsilane
  • methylvinyldiamidesilane eg, methylcarbodilu-N-ethylaminomethylvinylsilane.
  • Component (c) may be a single compound or a mixture of two or more types.
  • the amount of component (c) used should be such that cross-linking curing (particularly curing by moisture) occurs. It may be used. However, if the amount is too small, curing may be insufficient, and even if the curing is performed, the storage stability is poor.If the amount is too large, the effect of delaying the curing is remarkable, which may cause a problem in use. . Accordingly, the amount is usually from 0.01 to 50 parts by weight, preferably from 0.1 to 20 parts by weight, based on 100 parts by weight of the component (a).
  • the silicone resin composition in the first embodiment is a mixture of the component (a), the component (b) and the component (c).
  • the mixing causes a reaction between the components, and Part or all of each of (a) to (c) may be changed.
  • the OH group-containing polysiloxane of the component (a) reacts with the organic silicon cross-linking agent of the component (c), and the organic silicon cross-linking agent is bonded to the siloxane end. Even if they do not react, they may be partially reacted or all reacted.
  • reaction of the carbodiimide compound is not always clear, and both cases in which the reaction occurs and those in which the reaction does not occur are included in the scope of the present invention.
  • the silicone resin composition of the first embodiment is preferably cured by moisture to give a rubber-like cured product.
  • the silicone resin composition may contain, for example, a curing catalyst, a filler, an adhesion improving agent, and the like, if necessary, and these can be mixed using an ordinary kneader.
  • a curing catalyst for example, a filler, an adhesion improving agent, and the like, if necessary, and these can be mixed using an ordinary kneader.
  • the curing proceeds due to the moisture in the air, so it is necessary to replace with nitrogen in the kneader, and when storing the silicone resin composition in a container, it is necessary to store it in a closed container.
  • the curing conditions are the same as those for ordinary condensation type one-part silicone resin compositions, and are, for example, temperatures of 100 ° C. or lower, preferably 80 ° C. or lower, more preferably 60 ° C. or lower. Humidity below 10 ° C, for example in the range above 10 ° C, preferably above 0 ° C
  • the curing may be performed for 0.1 to 240 hours under the curing conditions of% to 100%. Usually, it may be performed in a normal atmosphere at room temperature or ambient temperature.
  • known fillers such as fumed silica, surface-treated fumed silica, precipitated silica, diatomaceous earth, quartz powder, calcium carbonate, calcium carbonate,
  • known fillers such as fumed silica, surface-treated fumed silica, precipitated silica, diatomaceous earth, quartz powder, calcium carbonate, calcium carbonate,
  • magnesium oxide, titanium oxide, iron oxide, silicates (or composite oxides) such as iron or aluminum, silane coupling agents as adhesion promoters, and organotin compounds as curing accelerators organic A titanium compound and an amine compound may be blended.
  • the component (d) described below may be mixed with the silicone resin composition of the first embodiment, but most of the component (d) often functions as a silane coupling agent when moisture is cured.
  • component (d) an amino group-containing silane compound in addition to component (a) and component (b).
  • silazane compound examples include linear silazanes and cyclic silazanes. Can be.
  • linear silazane compound for example, a compound represented by the general formula
  • R is H or an alkyl group, etc., r is 0 or 1 or more, for example an integer up to about 10)
  • R is H or a methyl group
  • r is 0 or 2.
  • R is H or an alkyl group, and r is 3 or more, for example, an integer up to about 10).
  • R is H or a methyl group, and r is 4 in a typical example.
  • amino group-containing silane compounds that can also be used as component (d) include, for example, 3- [N-aryl-1-N (2-aminoethyl)] aminopropyltrimethoxysilane, P- [N- (aminoethyl) amino Methyl] phenethyltrimethoxysilane, N— (2-aminoethyl) -13-aminopropylmethyldimethoxysilane, N— (2-aminoethyl) -13-aminopropylmethyldimethoxysilane, N—
  • 1,3_bis (chloromethyl) 1,1,3,3-tetramethyldisilazane ⁇ , ⁇ -bis [(methyldimethoxysilyl) propyl] amine, ⁇ , ⁇ -bis [3- (methyldimethoxysilyl) Propyl] ethylenediamine, ⁇ , ⁇ -bis [3- (trimethoxysilyl) propyl] amine, ⁇ , ⁇ -bis [3- (trimethoxysilyl) propyl] ethylenediamine, hexamethylcyclotrisilazane, hexamethyldisilazane Octamethylcyclotetrasilazane, tetramethyldisilazane, ⁇ — [(3-trimethoxysilyl) propyl] diethylenetriamine, ⁇ — [(3-trimethoxysilyl) propyl] triethylenetetramine, ⁇ —3— Trimethoxysilylpropyl 1
  • the amount of component (d) used may be such that the composition containing components (a), (b) and (d) is cured by heating, but too little may result in insufficient curing. Therefore, the amount is usually 0.01 part by weight or more, preferably 0.1 part by weight or more based on 100 parts by weight of the component (a). On the other hand, if the amount is too large, the physical properties of the obtained cured product may be remarkably deteriorated. Accordingly, the amount is usually, for example, 0.01 to 100 parts by weight, preferably 0.1 to 50 parts by weight, per 100 parts by weight of the component (a).
  • the silicone resin composition in the second embodiment is a mixture of the component (a), the component (b) and the component (d).
  • the mixing causes a reaction between the components, and Part or all of each of (a), (b) and (d) may be changed.
  • the component (d) is a silane coupling agent type
  • the alkoxy group portion may react with the OH group-containing polysiloxane of the component (a). It may be either partially reacted, all reacted, or any.
  • reaction of the carbodiimide compound is not always clear, and both cases in which the reaction occurs and those in which the reaction does not occur are included in the scope of the present invention.
  • the silicone resin composition of the second embodiment is cured by heating to give a rubber-like cured product.
  • the silicone resin composition may contain a curing catalyst, a filler, an adhesion improver, and the like, if necessary, and these can be mixed using a usual kneader.
  • the curing conditions are usually 20 ° C or higher, preferably 40 ° C or higher, for example, 50 ° C or higher, usually 250 ° C or lower, preferably 200 ° C or lower, for 0.1 hour to 24 hours. What is necessary is just to apply and harden.
  • a known filler such as fumed silica may be used, if necessary, to improve the physical properties of the silicone cured composition.
  • silane coupling agent as an enhancer and an organotin compound, an organic titanium compound, or an amine compound may be added as a curing accelerator.
  • the components (a), (b), (d) and the materials to be added as needed may be mixed before use, and may be stored as a mixed one-component type and distributed. It may be divided into two or more packs and stored as a two-pack or three-pack type. In particular, when the curing speed is fast, it is preferable to divide and store and distribute as a two-part type (or more than two parts). The division may be performed according to the purpose. For example, a two-pack type is divided into a pack containing the component (a) and the component (b) and a pack containing the component (a) and the component (d). be able to. At the time of use, it may be kneaded with a static mixer, a dynamic mixer, or the like, if necessary, and cured under the above-described curing conditions.
  • Example 1 Example 1
  • the test method was based on J IS K6258, and Mobil Oil Mobi 11 Turb 5W-50 SJ / CF (1000CC) was put in a glass container, and obtained in each Example and Comparative Example. Three dumbbell-shaped silicone cured products were placed in each case.
  • the test method is based on J IS K6258, and 1000 cc of Mitsubishi Motors Co., Ltd. Jacques Super Long Life is put in a glass container. Each of the three dumbbell-shaped No. 3 pieces obtained was inserted.
  • component (a) 20000 cp of OH-terminated polydimethylsiloxane and 6000 cp of OH-terminated polydimethylsiloxane (weight ratio 70:30)
  • Cab—O—Si TS530, calcium carbonate, carbon black, and iron'aluminum silicate were charged in the amounts shown in Table 1 and kneaded for 1 hour. Thereafter, the mixture was heated to 120 ° C and kneaded for another hour.
  • component (c) After cooling, it is filled with nitrogen, and tetra (methylethylketoximo) silane and vinyltri (methylethylketoximo) silane are used as component (c), and polycarboimide Carbod ilite V manufactured by Nisshinbo Co., Ltd. is used as component (b).
  • component (b) polycarboimide Carbod ilite V manufactured by Nisshinbo Co., Ltd.
  • the silicone rubber composition was charged into a Teflon-coated mold having a capacity of 15 cm ⁇ 15 cm ⁇ 0.2 cm, a release paper was placed thereon, and a flat mold was further placed thereon. At a pressure of 100 kgf / cm 2 for 1 hour. After removal, the flat mold was removed, and the silicone resin composition was cured in a constant temperature and humidity chamber at a temperature of 25 ° C and a humidity of 65% to obtain a cured rubber.
  • the component (b) was a polycarboimide Carbo di 1ite V_04B manufactured by Nisshinbo Industries, Ltd., and the component (d) was 3-aminopropyltriethoxysilane or N, N-bis [(methyldimethoxysilyl).
  • Propyl] amine was further charged in the amount shown in Table 5 and kneaded at 25 ° C for 1 hour to obtain a silicone rubber composition.
  • a 15 cm ⁇ 15 cm ⁇ 0.2 cm mold coated with the silicone rubber composition in Teflon. 55 g is charged into a mold having a tee, and a flat mold is further placed thereon, and pressed with a press at 80 ° C. at a pressure of 100 kgf / cm 2 for 1 hour to harden the silicone resin composition.
  • the cured rubber was obtained.
  • a silicone resin set was prepared in the same manner as in Examples 4 to 7, except that the composition was changed to the composition shown in Table 7.
  • the silicone resin composition containing the carbodiimide compound of the present invention has excellent elongation, heat resistance, oil resistance, and chemical resistance, which are characteristics particularly required for automotive applications, and anti-aging properties. It is possible to provide a silicone resin composition which gives a silicone cured rubber excellent in excellentness.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition de résine de silicone obtenue par compoundage de 100 parties en poids d'un polysiloxane hydroxylaté (ingrédient (a)) avec 0,1 à 200 parties en poids d'un composé carbodiimide (ingrédient (b)) et un agent de réticulation organosilicié (ingrédient (c)), cette composition étant ensuite durcie à l'eau. L'invention concerne, en variante, une composition résine de silicone obtenue par compoundage de 100 parties en poids d'un polysiloxane hydroxylaté (ingrédient (a)) avec 0,1 à 200 parties en poids d'un composé carbodiimide (ingrédient (b)) et un composé silane aminé (ingrédient (d)), cette composition étant ensuite thermodurcie. Ainsi, on obtient un caoutchouc de silicone durci ayant une excellente extensibilité, résistance à la chaleur, résistance à l'huile et résistance chimique, propriétés requises en particulier dans les applications automobiles.
PCT/JP2003/016751 2002-12-26 2003-12-25 Composition de resine de silicone WO2004058896A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003292811A AU2003292811A1 (en) 2002-12-26 2003-12-25 Silicone resin composition
EP03768240A EP1584660A4 (fr) 2002-12-26 2003-12-25 Composition de resine de silicone

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JP2002-377219 2002-12-26
JP2002377219A JP2004204146A (ja) 2002-12-26 2002-12-26 シリコーン樹脂組成物

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US (1) US6972314B2 (fr)
EP (1) EP1584660A4 (fr)
JP (1) JP2004204146A (fr)
AU (1) AU2003292811A1 (fr)
WO (1) WO2004058896A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021261147A1 (fr) * 2020-06-26 2021-12-30 デクセリアルズ株式会社 Composition de résine thermoconductrice et feuille thermoconductrice l'utilisant

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5068451B2 (ja) * 2005-11-24 2012-11-07 モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 室温硬化性ポリオルガノシロキサン組成物
US20080027164A1 (en) * 2006-07-31 2008-01-31 Illinois Tool Works, Inc. Reduced Odor RTV Silicone
JP2009254938A (ja) * 2008-04-14 2009-11-05 Nippon Shokubai Co Ltd 粒子の分級方法およびその方法を用いて得られる粒子
US8202928B2 (en) * 2008-08-13 2012-06-19 Continental Automotive Systems, Inc Amine-cured silicone compositions resistant to hydrocarbon fluid and uses thereof
US20100038859A1 (en) * 2008-08-13 2010-02-18 Temic Automotive Of North America, Inc. Method of preparing amine-cured silicone compositions resistant to hydrocarbon fluid and uses thereof
US8125784B2 (en) * 2008-08-13 2012-02-28 Continental Automative Systems, Inc. Seal apparatus and method of manufacturing the same
EP2196503B1 (fr) * 2008-12-12 2015-02-18 Nitto Denko Corporation Composition de résine de silicone thermodurcissable, résine de silicone, feuille de résine de silicone et leur utilisation
WO2013071078A1 (fr) 2011-11-10 2013-05-16 Momentive Performance Materials, Inc. Composition d'organopolysiloxane durcissable à l'humidité
US9523002B2 (en) 2011-12-15 2016-12-20 Momentive Performance Materials Inc. Moisture curable organopolysiloxane compositions
US9663657B2 (en) 2011-12-15 2017-05-30 Momentive Performance Materials Inc. Moisture curable organopolysiloxane compositions
US9527959B2 (en) 2011-12-29 2016-12-27 Momentive Performance Materials Inc. Moisture curable organopolysiloxane composition
TW201434882A (zh) 2013-03-13 2014-09-16 Momentive Performance Mat Inc 可濕氣固化之有機聚矽氧烷組成物
KR20160008584A (ko) 2013-05-10 2016-01-22 모멘티브 퍼포먼스 머티리얼즈 인크. 비-금속 촉매형 실온 수분 경화성 오가노폴리실록산 조성물
CN103319897A (zh) * 2013-06-06 2013-09-25 常熟市江南粘合剂有限公司 耐油硅酮密封胶生产工艺
JP6217584B2 (ja) * 2014-10-17 2017-10-25 信越化学工業株式会社 室温硬化性オルガノポリシロキサン組成物
JP6360586B1 (ja) * 2017-04-13 2018-07-18 三菱電線工業株式会社 Ｃｍｐ装置のウエハ保持用の弾性膜
CN107523064A (zh) * 2017-10-11 2017-12-29 惠州市臻晖电子有限公司 一种高抗黄的保护壳硅胶材料及保护壳的制作方法
CN110358299B (zh) * 2019-07-15 2021-04-02 浙江新安化工集团股份有限公司 一种杂化改性硅橡胶及其制备方法和应用

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2973334A (en) * 1956-10-17 1961-02-28 Ici Ltd Composition comprising an organopolysiloxane resin and a carbodimide
JPS5291100A (en) * 1976-01-23 1977-08-01 Bayer Ag Polysiloxaneepolycarbodiimido copolymer
JPS5417961A (en) * 1977-07-07 1979-02-09 Bayer Ag Organopolysiloxane improved with polycarbodiimide
JPS5562962A (en) * 1978-11-02 1980-05-12 Bayer Ag Organopolysiloxane elastomer containing polycarbodiimideepolysiloxane copolymer
JPS5562961A (en) * 1978-11-02 1980-05-12 Bayer Ag Organic polysiloxane contained composition
JPH0476058A (ja) * 1990-07-18 1992-03-10 Toshiba Silicone Co Ltd 室温硬化性シリコーンシール剤組成物
JPH107806A (ja) * 1996-06-25 1998-01-13 Japan Synthetic Rubber Co Ltd 熱硬化性樹脂組成物
US5741839A (en) * 1995-05-02 1998-04-21 Huels Silicone Gmbh Storage-stable alkoxy-crosslinking RTV1 systems
JPH1121443A (ja) * 1997-06-30 1999-01-26 Tonen Corp オルガノポリシロキサン系流体組成物
JP2002053759A (ja) * 2000-06-05 2002-02-19 Rohm & Haas Co 耐摩耗性コーティング組成物およびコーティングの製造法
JP2002226708A (ja) * 2001-01-30 2002-08-14 Three Bond Co Ltd 自動車用室温硬化性シール材組成物
JP2003174025A (ja) * 2001-12-07 2003-06-20 Hitachi Chem Co Ltd シリカ系被膜、シリカ系被膜形成用組成物、シリカ系被膜の製造方法及び電子部品

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2941956A (en) 1956-08-15 1960-06-21 Socony Mobil Oil Co Inc Regeneration of contact material
US3334067A (en) * 1966-04-08 1967-08-01 Dow Corning Method of making one component room temperature curing siloxane rubbers
US3689454A (en) * 1971-01-06 1972-09-05 Gen Electric Curable compositions

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2973334A (en) * 1956-10-17 1961-02-28 Ici Ltd Composition comprising an organopolysiloxane resin and a carbodimide
JPS5291100A (en) * 1976-01-23 1977-08-01 Bayer Ag Polysiloxaneepolycarbodiimido copolymer
JPS5417961A (en) * 1977-07-07 1979-02-09 Bayer Ag Organopolysiloxane improved with polycarbodiimide
JPS5562962A (en) * 1978-11-02 1980-05-12 Bayer Ag Organopolysiloxane elastomer containing polycarbodiimideepolysiloxane copolymer
JPS5562961A (en) * 1978-11-02 1980-05-12 Bayer Ag Organic polysiloxane contained composition
JPH0476058A (ja) * 1990-07-18 1992-03-10 Toshiba Silicone Co Ltd 室温硬化性シリコーンシール剤組成物
US5741839A (en) * 1995-05-02 1998-04-21 Huels Silicone Gmbh Storage-stable alkoxy-crosslinking RTV1 systems
JPH107806A (ja) * 1996-06-25 1998-01-13 Japan Synthetic Rubber Co Ltd 熱硬化性樹脂組成物
JPH1121443A (ja) * 1997-06-30 1999-01-26 Tonen Corp オルガノポリシロキサン系流体組成物
JP2002053759A (ja) * 2000-06-05 2002-02-19 Rohm & Haas Co 耐摩耗性コーティング組成物およびコーティングの製造法
JP2002226708A (ja) * 2001-01-30 2002-08-14 Three Bond Co Ltd 自動車用室温硬化性シール材組成物
JP2003174025A (ja) * 2001-12-07 2003-06-20 Hitachi Chem Co Ltd シリカ系被膜、シリカ系被膜形成用組成物、シリカ系被膜の製造方法及び電子部品

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1584660A4 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021261147A1 (fr) * 2020-06-26 2021-12-30 デクセリアルズ株式会社 Composition de résine thermoconductrice et feuille thermoconductrice l'utilisant
JP6997834B1 (ja) 2020-06-26 2022-01-24 デクセリアルズ株式会社 熱伝導性樹脂組成物及びこれを用いた熱伝導性シート
JP2022024210A (ja) * 2020-06-26 2022-02-09 デクセリアルズ株式会社 熱伝導性樹脂組成物及びこれを用いた熱伝導性シート
US11692118B2 (en) 2020-06-26 2023-07-04 Dexerials Corporation Thermally conductive resin composition and thermally conductive sheet using the same

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US20040127669A1 (en) 2004-07-01
US6972314B2 (en) 2005-12-06
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EP1584660A1 (fr) 2005-10-12
AU2003292811A1 (en) 2004-07-22
JP2004204146A (ja) 2004-07-22

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